CA1281842C - Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci - Google Patents

Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci

Info

Publication number: CA1281842C
Authority: CA; Canada
Prior art keywords: functional; functional component; percent; weight; less
Prior art date: 1986-01-14
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA 499562

Other languages

English (en)

Inventor

James L. Bertram

Louis L. Walker

Avis L. Mccrary

Fermin M. Cortez

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-01-14

Filing date

1986-01-14

Publication date

1991-03-19

1986-01-14 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1986-01-14 Priority to CA 499562 priority Critical patent/CA1281842C/fr

1991-03-19 Application granted granted Critical

1991-03-19 Publication of CA1281842C publication Critical patent/CA1281842C/fr

2008-03-19 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

229920003986 novolac Polymers 0.000 title claims abstract description 110
239000004593 Epoxy Substances 0.000 title claims abstract description 54
238000000034 method Methods 0.000 title claims abstract description 23
229920005989 resin Polymers 0.000 claims abstract description 36
239000011347 resin Substances 0.000 claims abstract description 36
239000000306 component Substances 0.000 claims description 87
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
239000000463 material Substances 0.000 claims description 17
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
150000001299 aldehydes Chemical class 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 claims description 8
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 8
238000000605 extraction Methods 0.000 claims description 6
235000006408 oxalic acid Nutrition 0.000 claims description 6
-1 glycol ethers Chemical class 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
150000003934 aromatic aldehydes Chemical class 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 claims description 3
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims 4
150000002118 epoxides Chemical group 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 18
229920001568 phenolic resin Polymers 0.000 abstract description 8
238000005266 casting Methods 0.000 abstract description 7
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract description 7
230000009477 glass transition Effects 0.000 abstract description 3
239000000853 adhesive Substances 0.000 abstract description 2
230000001070 adhesive effect Effects 0.000 abstract description 2
238000000576 coating method Methods 0.000 abstract description 2
239000002131 composite material Substances 0.000 abstract description 2
238000000465 moulding Methods 0.000 abstract description 2
ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 abstract 1
239000011248 coating agent Substances 0.000 abstract 1
239000000047 product Substances 0.000 description 41
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
150000002924 oxiranes Chemical group 0.000 description 24
230000000052 comparative effect Effects 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
238000005227 gel permeation chromatography Methods 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 10
239000003822 epoxy resin Substances 0.000 description 10
229920000647 polyepoxide Polymers 0.000 description 10
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 6
238000000113 differential scanning calorimetry Methods 0.000 description 5
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
239000000155 melt Substances 0.000 description 5
238000003809 water extraction Methods 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000003518 caustics Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
238000005292 vacuum distillation Methods 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
239000002970 Calcium lactobionate Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012265 solid product Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
229940043265 methyl isobutyl ketone Drugs 0.000 description 2
IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000005245 sintering Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000010998 test method Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
241001274660 Modulus Species 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
SRWLXBHGOYPTCM-UHFFFAOYSA-M acetic acid;ethyl(triphenyl)phosphanium;acetate Chemical compound CC(O)=O.CC([O-])=O.C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SRWLXBHGOYPTCM-UHFFFAOYSA-M 0.000 description 1
BZPUUPVCWNNZKW-UHFFFAOYSA-M acetic acid;tetrabutylphosphanium;acetate Chemical compound CC(O)=O.CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC BZPUUPVCWNNZKW-UHFFFAOYSA-M 0.000 description 1
HWZRXCHJIQVTPX-UHFFFAOYSA-N acetic acid;triphenylphosphanium;acetate Chemical compound CC(O)=O.CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 HWZRXCHJIQVTPX-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000002844 continuous effect Effects 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
238000007656 fracture toughness test Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Phenolic Resins Or Amino Resins (AREA)

CA 499562 1986-01-14 1986-01-14 Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci Expired - Fee Related CA1281842C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 499562 CA1281842C (fr)	1986-01-14	1986-01-14	Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 499562 CA1281842C (fr)	1986-01-14	1986-01-14	Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci

Publications (1)

Publication Number	Publication Date
CA1281842C true CA1281842C (fr)	1991-03-19

Family

ID=4132273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 499562 Expired - Fee Related CA1281842C (fr)	1986-01-14	1986-01-14	Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci

Country Status (1)

Country	Link
CA (1)	CA1281842C (fr)

1986
- 1986-01-14 CA CA 499562 patent/CA1281842C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1993-09-21	MKLA	Lapsed

Publication	Publication Date	Title
US3306872A (en)	1967-02-28	Method for producing a polyether resin
US3637590A (en)	1972-01-25	Thermoplastic polyether resins of bisphenols
US4649188A (en)	1987-03-10	Method for reducing 2-functional components in novolac resins and epoxy novolac resins prepared therefrom
WO1986004075A1 (fr)	1986-07-17	Resines novolac epoxy possedant des constituants a 2 fonctions reduits et un procede pour reduire les constituants a 2 fonctions dans les resines novolac
US4368299A (en)	1983-01-11	Epoxy resin compositions
CA1335402C (fr)	1995-04-25	Resines epoxydes halogenees avancees
US4755543A (en)	1988-07-05	Phenol-formaldehyde resins containing reduced quantities of 2-functional components and epoxy novolac resins prepared therefrom
KR900008962B1 (ko)	1990-12-15	트리글리시딜 에테르 및 2가 페놀로부터 제조된 개선된 에폭시 수지
KR940010010B1 (ko)	1994-10-20	페놀류 노볼락형 수지, 그 경화물 및 그 제조방법
EP0239784B1 (fr)	1992-05-06	Compositions durcissables contenant un polyépoxyde et un bisphénol halogéné
CA1281842C (fr)	1991-03-19	Methode pour la reduction de composes a groupe fonctionnel en 2 dans des resines novolac et dans des resines epoxydiques novolac preparees a partir de celles-ci
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US5106923A (en)	1992-04-21	Substituted phenol-formaldehyde novolac resins containing reduced quantities of 2-functional components and epoxy novolac resins prepared therefrom
KR900008462B1 (ko)	1990-11-22	비-소결 에폭시수지 및 이의 제조방법
US5151496A (en)	1992-09-29	Substituted phenol-formaldehyde novolac resins containing reduced quantities of 2-functional components and epoxy novolac resins prepared therefrom
US5079314A (en)	1992-01-07	Curable compositions containing epoxidized phenolformaldehyde resins containing reduced quantities of 2-functional components
EP0232910B1 (fr)	1990-04-25	Procédé pour la préparation de résines époxydes ou phénoxydes avec une faible teneur en halogène aliphatique
US4755568A (en)	1988-07-05	Substituted phenol-formaldehyde novolac resins containing reduced quantities of 2-functional components and epoxy novolac resins prepared therefrom
JP3074013B2 (ja)	2000-08-07	エポキシ樹脂組成物及びその硬化物
US4965324A (en)	1990-10-23	Substituted phenol-formaldehyde novolac resins containing reduced quantities of 2-functional components and epoxy novolac resins prepared therefrom
AU595381B2 (en)	1990-03-29	Blends of relatively low molecular weight epoxy resins and relatively high molecular weight epoxy or phenoxy resins and cured products therefrom
JP2003137950A (ja)	2003-05-14	ジヒドロキシベンゼン型ノボラック樹脂の製造方法、エポキシ樹脂組成物及びその硬化物。
EP0458417A2 (fr)	1991-11-27	Adduits à base de composés chimiques phénoliques et de terpènes cycliques et dérivés de ces adduits
EP0582758B1 (fr)	1997-01-02	Dérivés de naphthalène contenant des groupes propényles et compositions de résine durcissable les contenant